Enantioselective synthesis of four isomers of 3-hydroxy-4-methyltetradecanoic acid, the constituent of antifungal cyclodepsipeptides W493 A and B.

Four possible stereoisomers of 3-hydroxy-4-methyltetradecanoic acid were enantioselectively synthesized by using Sharpless epoxidation and a subsequent epoxide-ring opening reaction with trimethylaluminum as the key steps. The absolute configuration of the double down arrow-oxyacid component of antifungal cyclodepsipeptides W493 A and B was consequently determined as 3S,4R.